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- Title
New Multiresponsive Chromic Soft Materials: Dynamic Interconversion of Short 2,7-Dicyanomethylenecarbazole-Based Biradicaloid and the Corresponding Cyclophane Tetramer.
- Authors
Wang, Deliang; Capel Ferrón, Cristina; Li, Jie; Gámez-Valenzuela, Sergio; Ponce Ortiz, Rocio; López Navarrete, Juan T.; Hernández Jolín, Víctor; Yang, Xiaodi; Peña Álvarez, Miriam; García Baonza, Valentín; Hartl, František; Ruiz Delgado, M. Carmen; Li, Hongxiang
- Abstract
This work reports on a quinodimethane-type molecule, 2,7-dicyanomethylene-9-(2-ethylhexyl)carbazole ( 1), one of the shortest π-conjugated biradicaloids reported to be stable in solution under ambient conditions. This carbazole-based quinoidal precursor is able to form a macrocyclic σ-bonded tetramer ( 2). The resolved single-crystal X-ray structure of tetramer 2 shows that four molecules of 1 are linked together through four long (CN)2C−C(CN)2 bonds (1.631 Å) resulting from coupling of the unpaired electrons in biradicaloid 1. Dynamic interconversion between monomer 1 and cyclophane tetramer 2 is achieved by reversible cleavage and recovery of the four (CN)2C−C(CN)2 bonds upon soft external stimuli (light absorption, temperature and pressure), which is accompanied by significant color changes. These novel photo-, thermo-, and mechanochromic properties expand the versatility of π-conjugated biradicaloid compounds as novel functional materials that, in combination with spin chemistry and dynamic covalent chemistry, can be relevant in molecular machines, sensors, and switches.
- Subjects
CHROMIC materials; CARBAZOLE; RADICALS (Chemistry); CYCLOPHANES; TETRAMERS (Oligomers)
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 55, p13776
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201702659